1. field of Invention
This invention relates to novel .alpha.-hydrazinocarboxamide and .alpha.-(.alpha. '-acylhydrazino)carboxamide derivatives, to processes for their preparation and to their use as intermediates for the preparation of related derivatives.
2. Description of the Prior Art
Only within the last ten years has some attention been focused on .alpha.-hydrazinocarboxamides. This attention resulted from a chemical investigation by I. Ugi and F. Bodesheim, Justus Liebigs Ann. Chem., 666, 61 (1963). In this particular investigation .alpha.-(.alpha. ', .beta.'-diacylhydrazino)carboxamides were prepared by the .alpha.-addition of acylhydrazones and carboxylic acids to isonitriles. The carboxamides of this latter study are readily distinguished from the compounds of the present invention by their lack of a basic nitrogen.
Indeed, the successful preparation of the present .alpha.-(hydrazino)- and .alpha.-(.alpha.'-acylhydrazino)caboxamides from hydrazones, acids and isonitriles is somewhat unexpected and surprising in light of a recent comment by Ugi. More explicitly, in "Newer Methods of Preparative Organic Chemistry", Vol. IV, N. Foerst, Ed., Academic Press, New York and London, 1968, p. 28, Ugi states that the lower basicity of the .alpha.-nitrogen in a hydrazone system has an adverse influence on .alpha.-additions involving hydrazones and it may be assumed that such reactions can rarely be used for preparative purposes.